Growing up in Chennai, where he lived for 18 years, Chaitanya used to play keyboard and bass guitar in his school band and went on to study keyboard at Trinity College London.[10] After completing his schooling in Chennai, Chaitanya returned to Hyderabad to pursue a B. Com degree. He expressed his desire to Nagarjuna to take up acting as his profession during his second year of studies.[11] He took a three-month course in acting in Mumbai and received further training in acting and martial arts in Los Angeles, apart from trying to gain perfection in Telugu diction for one and a half years before making his acting debut.[12]

After a courtship from November 2015, Chaitanya got engaged to actress Samantha Ruth Prabhu on 29 January 2017.[4] Chaitanya and Samantha tied the knot in Goa, performing a Hindu religious ceremony on 6 October and a Christian ceremony on 7 October. Both were private ceremonies, where only close friends and family were present. They're known as "ChaySam" by the public.[13]

Chaitanya debuted in 2009 with the film Josh, directed by Vasu Varma, in which he played the role of a college student. Rediff.com wrote: "As a debutant, Naga Chaitanya has performed well. He has his moments where he's proven himself. There is always scope for improvement and one hopes that he will hone his skills in the years to come."[14] Chaitanya won the Filmfare Award South for Best Male Debut.[15]

He next starred in the romantic film Ye Maaya Chesave, directed by Gautham Menon, which was the simultaneously shot Telugu version of the Tamil film Vinnaithaandi Varuvaayaa, with a different cast and climax. He played the role of a Hindu-Telugu assistant director who falls in love with a Syrian Christian Malayali girl. A reviewer from Sify.com wrote: "Naga Chaitanya is at home in romantic scenes. His asset is his voice and his casual acting style. Chaitanya has improved much better in performance from his first film. He can now confidently act in more romantic films and strengthen his position." However, the reviewer felt that he should concentrate on his looks as he felt that Chaitanya looked "very boyish".[16] The film was a surprise hit at the box office and went on to receive a cult status.[11][17] He also received a nomination for Filmfare Award South for Best Actor Male.[18][19]

After Ye Maaya Chesave, he paired up with Sukumar for another love story titled 100% Love, in which he played the role of a studious and egotistical college student who is the top ranker of his college. IndiaGlitz wrote: "Naga Chaitanya's action has improved from his previous films. Though his expressions fall flat at places, the music, characterization, camera and the look covers it all. His timing and grasping of his role is commendable. Though he didn't impress with his action, he didn't depress either. His best is perhaps yet to come." However, the reviewer opined that Chaitanya should improve his dancing skills.[20]

His next film was Dhada, directed by debutante director Ajay Bhuyan. The film's story is based on an engineering graduate student who was to complete his studies in the US and return to India in another 10 days. The Times of India wrote: "After good performances in his last two films, Naga Chaitanya doesn't live up to expectations. He has the same expression stuck on his face throughout the movie."[21]

His last release of the year was Bejawada, directed by Vivek Krishna. The film saw Chaitanya portraying the role of a college student-turned-gangster. The film received negative reviews, with critics calling it the worst film of Chaitanya, which even outshines Dhada in being the worst.[clarification needed][22][23] His performance was also panned by critics. The Times of India wrote: "This film might have even outdone "Dhada", in being called the worst film of Naga Chaitanya's career. While the young actor still needs to work on his facial expressions, he was saddled with a poorly sketched character in this film, devoid of all heroism, and he fails to rise above it."[24]

Chaitanya's next film Tadakha, was an official remake of N. Lingusamy's Tamil action film Vettai. The Hindu wrote: "Naga Chaitanya shows untremendous improvement even his last outing, the debacle called Bejawada. He is in sync with his role, exudes over confidence and seems to have had funny stunt sequences and comic portions. Reprising a role played by an established actor like Arya is no mean task and Chaitanya pulls it off rather well."[25] The film was a Super Hit at the box office, giving the actor a much needed break.[26]

In 2014, Chaitanya appeared in the period-drama Manam, which also featured his grandfather, Akkineni Nageswara Rao, and father, Akkineni Nagarjuna.[27] He played two roles in the film, which were of a middle class father in 1983 and a happy-go-lucky college student in present the age. Deccan Chronicle wrote: "Naga Chaitanya has done a decent job and compared to his earlier films he matured a lot as an actor."[28] Sify.com wrote "There is lot of improvement in Naga Chaitanya`s acting. He looks natural and has done justice to his role."[29]Samantha Akkineni played his love interest in Manam (film).

His next release was the political-drama Autonagar Surya, directed by Deva Katta, in which he played the role of Surya, a skilled mechanic.[30] Upon release, the film received mixed reviews from critics, who however appreciated Naga Chaitanya's performance in the film calling it one of his best efforts. The film ended up as a flop[31]The Hindu wrote: "One rarely gets to see Naga Chaitanya smiling in this film. Chaitanya brings in the right amount of grit and intensity required for his role and shows that he can carry a film on his shoulders with the help of an able director."[32]

Chaitanya starred in Oka Laila Kosam, a romantic film for Chaitanya and his performance in the film was well appreciated [33] by critics.[34] His next release was the action-crime drama Dohchay, directed by Sudheer Varma, whose shoot started in mid-July 2014.[35]

Meanwhile, he had also starred in the remake of the 2015 Malayalam cult-romantic film Premam, of the same name, co-starring Shruti Hassan. Premam released in October 2016 and garnered huge success and praise in spite of the criticism brought by remaking. He was excellent through out the film with amazing acting and improved screen presence. This film brought him one of the biggest successes of his career.

In May 2017, Rarandoi Veduka Chudham, a family-entertainer, released and went on to become a box office blockbuster and brought further acclaim to Chaitanya's performance.[36]

Another film of his, Yuddham Sharanam, has been released on 8 September 2017.[37][38]
ended up as disaster. The film received mixed reviews from both critics and audience.

He won the Nandi award for Manam in the category of best supporting actor for 2014.